Brett Trainor Unplugged

Jon the Escapee Collective!

What keeps 79% of corporate professionals stuck isn't lack of skills or opportunity—it's something deeper. In this solo episode, Brett shares the story of landing his first client, making good money, and then doing something that still makes him cringe: convincing that company to hire him full-time. Nobody forced him back. He walked himself in.

This mistake cost him 18 months and taught him the hard truth: leaving corporate is tactical, but breaking your dependency on it is psychological. Brett breaks down what corporate dependency actually is (hint: it's not just the paycheck), why going solo alone reinforces that dependency, and the two critical milestones that finally sever the tie.

If you're still in corporate and thinking about making a move—or you've already left but still feel the pull—this episode will help you understand what you're really up against and how to break free for good.

What You'll Learn:

Key Quotes:

Resources Mentioned:

The Escapee Collective: Join Brett's community

Subscribe & Connect: If this episode resonated with you, please subscribe to The Corporate Escapee Podcast on your favorite platform. New episodes drop multiple times per week featuring guest interviews and solo deep-dives like this one.

Looking to break your corporate dependency? Visit TheEscapeeCollective.com to connect with others on the same journey.

Corporate isn’t stabilizing—and that matters if your income still depends on it.

In this solo episode, Brett breaks down three trends shaping the Escapee economy in 2026:

If you’re still in corporate, this episode helps you see what’s coming.

If you’ve already escaped, it explains why demand for your experience is only growing.

This episode is for you if:

The 3 trends covered in this episode

Trend #1: The metric driving modern layoffs — Revenue Per Employee (RPE)

Why boards and executives are fixated on RPE, how it incentivizes headcount reduction, and why even “healthy” companies continue cutting roles.

Trend #2: The explosion of revenue streams for escapees

Fractional leadership, consulting, advisory, UGC, content creation, mentoring, and more—why monetizing what you already know is the fastest, lowest-friction path to income.

Trend #3: The small business go-to-market model is changing

Why businesses are ditching traditional silos, hiring specialists instead of full-time staff, and how this shift creates long-term opportunity for experienced operators.

Key takeaways

• Corporate risk is structural, not cyclical

• Escapees have more income options than they think

• Small businesses want outcomes, not headcount

• Your experience is often more valuable outside corporate than inside it

If this episode helped you rethink corporate risk or life after it, connect with Brett on LinkedIn or email him at [email protected]. And if there’s a topic you want covered in a future solo episode, let him know.

Ashley Evenson returns for her third appearance on The Corporate Escapee Podcast — and this time it’s a real update from the field. Two years into her escape, she breaks down what actually helped her land fractional work, what surprised her, and the biggest mistake most new escapees make once they get busy.

This is a practical conversation about network-first business development, creating momentum without feeling “salesy,” and why the long game matters more than the perfect plan.

What you’ll learn

• How Ashley landed her first fractional roles through her existing network

• Why “pick your brain” beats cold outreach for most escapees

• The content → connection flywheel: using LinkedIn engagement to reopen relationships

• What fractional work can feel like behind the scenes (and why it can get lonely)

• How Ashley uses frameworks + a single grounding slide to lead discovery conversations

• Why you must keep “breadcrumbing” even when client work gets busy

• The reality of income volatility — and how to reduce the “oh crap” moments

• Portfolio career thinking: experimenting with speaking, books, and new revenue streams

• A fun (and honest) AI/TikTok viral experiment — and what it taught her about unit economics

• The mindset truth: escaping requires hustle — but it’s a better “hard” than corporate

Key quotes

• “You’re in here for the long game.”

• “People are sick of being sold to on LinkedIn.”

• “Always be top of mind… keep breadcrumbing.”

• “Both paths are hard. Choose which hard you want.”

Resources & mentions

• Connect with Ashley on LinkedIn: https://www.linkedin.com/in/ashleyevenson/ 

• Ashley’s site: AE Marketing Collective: aemarketingcollective.com

• AI slide tool mentioned: Gamma (export to Google Slides / PowerPoint)

If this episode hit home…

If you’re still in corporate and thinking about an exit strategy:

• Start with one conversation this week.

• Don’t pitch. Ask for perspective.

• Keep one weekly “breadcrumb” habit so you don’t disappear when you get busy.

About the guest

Ashley is a fractional marketing leader with experience across agency, brand, and consul

Corporate gives you an easy identity: your title, your company, your lane. But once you start building something outside corporate—consulting, fractional, content, a book, a business—that identity disappears fast. And that’s where most people get stuck.

In this episode, Brett sits down with Catherine Jelinek, founder of The Skinny Platform, to talk about the shift from being “defined by your role” to being known for your thinking, your story, and the outcomes you create.

Catherine shares why so many high-performing corporate pros struggle in the “formless” world outside corporate, how to create structure without recreating corporate, and why the fastest way to clarify your thought leadership is often talking it out—not trying to write it alone. They also get into “skinny books” (short, high-impact nonfiction) and how to use AI and conversation-based drafts to accelerate publishing and content creation.

What You’ll Learn

• Why corporate identity feels safe—even when corporate is miserable

• How to replace “job title identity” with outcome-based positioning

• Catherine’s framework for navigating change: Forming → Storming → Norming → Performing

• How Brett created structure outside corporate (without turning life into a calendar prison)

• Why most people can’t “see” their own differentiators—and how a mirror helps

• Why conversation + transcripts can be the fastest path to content (and even a book)

• The “skinny book” approach: short, readable, practical nonfiction that people actually finish

• How to use AI to generate multiple story arcs and content angles—without losing your voice

Key Takeaways

• You don’t need to reinvent yourself. You need to reframe yourself.

• Progress outside corporate isn’t linear—so you need your own way to measure wins.

• If you want thought leadership, stop trying to “perfect-write” it. Talk it out first.

• Your story isn’t just for a book. It can power your LinkedIn, website, offers, and messaging.

About Catherine Jelinek

Catherine is the founder of The Skinny Platform, an alternative to ghostwriting for entrepreneurs and thought leaders. The Skinny Platform helps people clarify their story, shape it into a compelling narrative, and turn it into a short, high-impact book—faster than the traditional publishing process.

Connect with Catherine

• https://www.linkedin.com/in/cjelinek/

• Email: [email protected]

• Websites: theskinnyplatform.com

Post Corporate Life with Brett Trainor & John Arms

I recently had the chance to join John Arms on his podcast: Fractional Unfiltered Link: https://open.spotify.com/episode/0z9pQOOMZEVI4T2NvoOiqP?si=uJoycF4LRGyZQNB4MofrtQ

John was kind enough to allow me to share this with my audience.

Corporate has done a number on people. A bad one. For 30 minutes we bitch about what is and was, and then we spend 30 minutes on how to thrive in the post corporate world.

This episode also includes real-time audience coaching around “job hugging,” starting from zero, and how to simplify your entry point so you can land your first client.

If corporate feels unstable — don’t wait for it to get personal. Start building momentum now:

Most people believe the ones who succeed after escaping corporate are the smartest, most experienced, or most credentialed.

They’re not.

In this solo episode, Brett breaks down a pattern he’s seen across hundreds—if not thousands—of conversations with corporate escapees: success outside corporate has far less to do with talent and far more to do with action.

This episode is for anyone still in corporate, recently laid off, or quietly wondering if there’s another path—but feeling stuck, underqualified, or unsure where to start.

What You’ll Learn in This Episode

• Why the most talented corporate professionals often struggle after leaving

• The real traits shared by people who successfully escape—and stay out

• Why overthinking your offer is one of the biggest mistakes escapees make

• How job interviews and client conversations are essentially the same thing

• Why “sales” after corporate is really just problem-solving

• How small wins (not big plans) create momentum

• Why redefining success becomes inevitable once you regain control of your time

• How to safely test a solo path while still in corporate—or during a job search

Key Takeaways

• You don’t need more experience to get started—you need movement

• Confidence comes after action, not before

• Business owners care about outcomes, not job titles

• Your network is your greatest advantage if you’re willing to use it

• The biggest risk isn’t trying—it’s never testing what’s possible

If You’re Still in Corporate (or Recently Laid Off)

You’re not behind.

You’re not underqualified.

And you already have skills people will pay for.

The fastest way forward isn’t a perfect plan—it’s one conversation.

Join the Escapee Collective

If you’re tired of figuring this out alone, the Escapee Collective is a community for corporate castaways and escapees at every stage—still in corporate, newly out, or building momentum.

Peer groups. Live sessions. Real conversations. Real progress.

You can find the link in the show notes or visit TheEscapeeCollective.com to learn more.

Michelle Warner took the “escapee avoidance” route — she planned to do the traditional MBA-to-consulting path… then graduated straight into the Great Recession (the day Lehman fell). That curveball pushed her into entrepreneurship early: a founder-for-hire role turning a multi-billion-dollar foundation asset into a business, followed by a mission-driven tech startup, and eventually her current work helping small business owners design the next iteration of their business.

This is a tactical episode about what actually works when you’re leaving corporate: why you should “throw spaghetti at the wall” early, how to stop doing random coffee chats, and how to use relationship marketing and audience borrowing to land clients faster — without turning into a sales robot.

What you’ll learn

• Why “sequence over strategy” matters more than the perfect plan

• The hidden risk of being too strict and narrow early on (and why it creates regret later)

• How Michelle built her business through relationship marketing, not content churn

• “Audience borrowing” as the fastest way to build trust and pipeline

• How to approach connector conversations vs. client conversations

• Why your early goal is simple: learn how to make money and stack wins

• A practical way to think about packaging: repeatable frameworks, flexible middle

Key moments / highlights

• Graduating into chaos: the day Lehman fell and what it changed

• Founder-for-hire: getting a salary while living the startup founder life

• Affordable internet in inner cities — and what customers actually did with it

• “Fractional CEO” before fractional was trendy

• The rule: don’t build with blinders on for too long

• The shift from “networking for jobs” to networking as a long-term business asset

• The line that matters: say something that people can’t “unsee” after the call

Michelle’s core concepts (worth stealing)

• Sequence over strategy: the order of moves beats the elegance of the plan

• Throw spaghetti first: test offers, clients, and problems before you commit

• Connection avatar: define who’s worth meeting so networking doesn’t waste your life

• Trust transfer: get introduced through people/places your audience already trusts

• Audience borrowing: build relationships with people who “own the room” your clients are in

Best quote energy

• “Learn all the rules so you can go break them.”

• “It’s more important the order you do things than how good you are at it.”

• “I’m totally unemployable.” (Escapee anthem)

Connect with Michelle

• Website: themichellewarner.com

• Podcast: Sequence Over Strategy (short, practical episodes; curated playlists on her site)

Connect with Brett / The Escapee ecosystem

• If corporate is broken and you’re looking at an exit strategy, this is your sign.

• Join the community: TheEscapeeCollective.com

If you’ve been thinking about leaving corporate but the risk feels too big, this episode gives you a smarter way to look at it.

Brett sits down with Alex Smereczniak, a former EY consultant who left corporate early, built a high-growth business in the laundry space, and later launched Franzy—a platform designed to make franchising easier to research and navigate.

This conversation covers the mindset shift that helps people stop overestimating the risk of leaving, plus why franchising can be an underrated “business with guardrails” path for escapees who want ownership without building from scratch.

What we cover

• Alex’s escape story: college entrepreneurship → EY → leaving after a year and change

• The moment that validated his decision: an EY partner’s biggest career regret

• Why fear is often self-created—and how to get past it

• A practical worst-case scenario exercise to reset your risk tolerance

• Why franchising is a business model, not an industry

• Franzy’s concept: “Zillow for buying and selling franchise businesses”

• How AI + coaching can narrow thousands of franchise options into a realistic short list

• Underrated franchise categories and trends (senior care, home services, turf, and more)

• The “corporate is one customer” reframe—and why ownership builds equity

Key timestamps (approx.)

• 00:00–03:30 – Alex’s corporate stint + why he left fast

• 03:30–08:30 – The EY exit interview story: “It wasn’t my ladder”

• 08:30–12:30 – Why making money outside corporate is more possible than people think

• 12:30–20:30 – The worst-case scenario exercise (the fear-killer)

• 20:30–28:30 – Alex’s journey building a scaled laundry business + why franchising clicked

• 28:30–33:30 – What franchising actually is (and what most people misunderstand)

• 33:30–40:30 – Franchise categories you probably haven’t considered

• 40:30–46:30 – Equity, control, and why “owning” beats “leasing” your career

Big takeaways

• Most people overestimate the risk of leaving corporate. The real risk is staying dependent on one employer.

• You don’t need a perfect plan. You need small wins and momentum—then you adjust.

• Franchising can be a fast path to ownership because you start with a proven playbook, support, and guardrails.

• Ownership builds equity. A job pays you, but it doesn’t typically create an asset you can sell.

Who this episode is for

• Corporate pros who want out but feel stuck because of risk, family, or finances

• Escapees who want a “business with guardrails” instead of starting from scratch

• Anyone curious about franchising beyond the usual fast-food stereotypes

Resources + links

• Franzy https://franzy.com/

• Alex on LinkedIn: https://www.linkedin.com/in/alex-smereczniak-40310329/

Tom Mirabella left corporate at 30 and never looked back. Seventeen years later, he’s built Wingman into a 25-person business by doing what corporate rarely rewards: solving problems fast, betting on relationships, and staying obsessively close to customers.

In this conversation, Tom breaks down his escape story, why “local + in-person” is making a comeback, and how Wingman’s franchise model flips the typical franchise script — where the franchisee focuses on relationships and sales while the central team handles fulfillment and delivery.

If you’re stuck in corporate and can’t see a path out, this episode gives you a practical look at what “building your own lane” can really look like — without pretending it’s easy.

Join the Escapee Collective: TheEscapeeCollective.com

What You’ll Learn

• Why Tom left corporate early (and what corporate policies taught him about ceilings)

• The side-hustle-to-business path: how one small project turned into real clients

• How to think about risk when leaving: your monthly “number” vs. replacing a salary

• Why entrepreneurship can swing from best day to worst day in 30 minutes — and how to handle it

• The “digital mayor” concept: becoming the trusted local hub in your town

• Why Tom believes physical locations + community presence still win in a digital world

• A modern franchise approach: franchisee sells + builds relationships, HQ team delivers

• Why customer service and trust are the real differentiators in crowded markets

Key Quotes

• “The problem’s now. Two weeks from now, it’s worse.”

• “As an entrepreneur, you can have the best and worst day within a half hour.”

• “I want you to be the digital mayor of your town.”

• “If you do what you love, the money follows.”

Mentioned in This Episode

• COBRA and how Tom thought about early-stage risk

• Networking groups, chambers, community events, and “planting seeds”

• Using a podcast as a lead generator (and why it worked)

Connect with Tom

• Email: Tom at wingmanplanning.com

• Website: WingmanPlanning.com

• Social: Instagram / Facebook / TikTok / LinkedIn (search “Wingman Planning”)

What if scaling your business didn’t require hiring, hustling harder, or stacking endless clients?

In this episode, Brett sits down with Pia Silva (No BS Mastery) to break down a simple model for building a highly profitable solo (or two-person) business — built around intensives, clear boundaries, and pricing for outcomes (not hours).

Pia shares how she and her husband went from $40K in debt to $500K in revenue by shifting from long, drawn-out projects to a focused, high-value intensive model. Then she explains her signature framework — the 50-25-25 Rule — and how to reverse-engineer your pricing based on the life you actually want.

If you’re a corporate escapee (or future one) trying to make real money without recreating the corporate grind… this is the blueprint.

What you’ll learn

• Why most “big ticket” projects are often the least profitable

• Pia’s 50-25-25 Rule for profit + freedom (and how to use it to price your offers)

• How to design offers so you make your monthly revenue in 50% of your client hours

• The two levers to grow profit without working more:

• Increase value (real + perceived)

• Decrease time (intensify delivery)

• A smarter version of “good / better / best” packaging (without selling deliverables)

• How to use a Lead Product (paid) instead of free proposals to build trust fast

• Why warm networks beat websites and content in the early stages

• How to build boundaries that prevent scope creep (without sounding rigid)

• The mindset shift escapees must make: sell outcomes, not time

Key frameworks + concepts mentioned

• The Intensives Model: Focused delivery in a compressed timeframe vs. dragging projects out for months

• 50-25-25 Rule: Make your total revenue in 50% (or less) of your client-working hours so you have time for life

• Lead Product Method: A paid diagnostic/strategy step that replaces proposals and tees up an easy upsell

• Boundaries via Process: Clear steps + expectations reduce pushback and scope creep

Resources from Pia

• Scale Solo Playbook: NoBSMastery.com/playbook

• Price to Freedom Calculator

Connect with Pia

• Instagram: @pialovesyourbiz

• LinkedIn: Pia Silva